Continous prompting in Outlook Anywhere
I had not brought this up as I thought RU5 was suppose to have the fix in it however I just was on a call and it sounds like this was never added to the current RU.
There is an issue when you enabled NTLM authentication in Outlook Anywhere when Exchange is installed on Windows 2008.
By default, Kernel Mode Authentication is enabled in IIS 7.0 on the Client Access server (CAS). To resolve this issue, disable Kernel Mode Authentication for Client Access servers that are running Windows Server 2008
1. open a command prompt window
2. cd \%systemroot%\system32\inetsrv\
3. AppCmd.exe set config /section:system.webServer/security/authentication/windowsAuthentication /useKernelMode:false
When you have the Outlook Anywhere feature configured on a Windows Server 2008-based computer that is running Terminal Services Gateway, you may experience the following symptoms:
- If you enable Outlook Anywhere before you install Terminal Services Gateway, users cannot connect to their Exchange mailboxes by using RPC over HTTP.
- If you enable Outlook Anywhere after you install Terminal Services Gateway, Outlook Anywhere users can connect to Exchange by using RPC over HTTP. However, after you open the TS Gateway Manager snap-in, Outlook Anywhere users can no longer connect to Exchange by using RPC over HTTP
http://technet.microsoft.com/en-us/library/bb123889.aspx

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February 8th, 2009 at 5:13 am
[...] Continous prompting in Outlook Anywhere [...]
January 27th, 2010 at 7:33 am
Hello,
When my exchange 2k10 CAS server is down, outlook prompt for credential. If user do nothing, the prompt stay and outlook is not updated.
Even with NLB, multi CAS,… the issue is there. I’ve tried to tweak registry, web server without success.
As someone see this when doing CAS failover ?
Regards,
Nicolas
January 27th, 2010 at 8:44 am
that should not be the case, what roles are on your CAS server. Most of the time when I have seen logon prompts it was related to accessing the public folder server.
January 27th, 2010 at 9:32 am
This is my configuration:
2x CAS server (doing HUB too) and NLB feature
linked to
2x CAS(maybe I’ll remove it), HUB, MBX doing DAG
I’ve tried different setups, most are using Anywhere. If I reboot the CAS used by outlook, I have a credential prompt.
In the meantime I’ve found that some outlook that don’t use RPCoverHTTP are not setup to use NTLM, I need to make tests to see if switching to NTLM solve the problem (for those ones).
Currently, public folder are still hosted on a 2k3 server.
January 30th, 2010 at 9:56 am
1. the the clients getting prompted you validated they are connecting with rcp.https?
look over this article I wrote about outlook anywhere http://www.exchange-genie.com/2008/02/configuring-outlook-anywhere-for-exchange-2007-sp1/
as it may assist…
March 7th, 2010 at 12:06 am
For the record — the bug is still present in Exchange 2010, Windows Server 2008 R2. And the workaround still works.
Earliest mention I can find of this problem is June 24, 2008. It’s now almost two years later! New version, new OS, *still* not fixed.